Bossnass hit the nail on the head about legal drinking ages in Canada: they alternate from province to province.
As for what to drink, try Quebec beer. None of that Moosehead, Alexander Keiths stuff (sorry, Rockzilla). You'll be in Quebec, so try the local stuff. If it's a French name, it's probably from Unibroue, a top-notch brewer where I'm from. Try "La Fin du Monde" ("The End of the World" - 9% Alcohol) or "La Maudite" ("The Damned" - 8% alcohol) and get ready to party.
If you're looking for strip clubs, dress nice and check out Wanda's. In my opinion, it's Montreal's best titty bar. 3 floors, all the girls are hot, lap dances are not private and you can't touch, but it's still worth it. Bands on tour always go there. Also, try Chez Pare, which is where the Montreal Canadiens (go Habs!) go for some downtime. Same rules as Wanda's: dress nice, act nice. And for god's sake, don't put loonies (1$ coins) on the fucking stage. I've seen many Americans do this. As a matter of fact, don't put any bills on any stage. Strippers make their money with lap dances only. Drinks WILL be horribly expensive (by Canadian standards) and only common beer (Molson, Labatt) will be available, so stick to mixes, like a good White Russian (vodka/kaluha/milk - goes down smooth) or CC7 (Canadian Club whiskey and 7up).
For clubs, check out St-Laurent street. For concert venues, check any local free publications and head for St-Denis street. "Le Swimming" (St-Laurent) has great live music and pool. "Casa Del Popolo" (St-Denis) has great food and some live shows. Also, the Sala Rossa, right across the street, has more eclectic shows. Montreal is known for that stuff, so be sure to check it out.
I could go on and on, since I'm from there, so PM me if you want more.
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